Find cheap flights from Hawaii to Chicago

Find cheap flights from Hawaii to Chicago

Round-trip
Economy
Boston (BOS)
Chicago All airports
Tue 8/4
Tue 8/11
Any month
Compare vs. KAYAK |
Search hundreds of travel sites at once for deals on flights to Chicago

Good to know

Low season

November Best time to beat the crowds with an average 5% drop in price.

High season

March Most popular time to fly with an average 12% increase in price.

Average price of a round-trip

$479 (avg. price over the last 2 weeks)

Good deal for a round-trip

$311 or less

FAQs for booking Hawaii to Chicago flights

How does KAYAK find such low prices on flights from Hawaii to Chicago?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?

What is the Hacker Fare option on flights from Hawaii to Chicago?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?

Top {4} airlines serving from Hawaii to Chicago

Scores according to KAYAK customer reviews

8.0
Delta
Overall score based on 28,492 reviews
8.2
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews
Read more about Delta

Book cheap flights from Hawaii to Chicago (round-trip)

Airports
Origin
Kahului
$367
only
$367
Honolulu
$315
only
$315
Lihue
$504
only
$504
Kailua-Kona
$542
only
$542
Destination
Chicago
$315
only
$315
Tue, Aug 25
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
19h 37m
Tue, Sep 8
ORD
Chicago O'Hare Airport
HNL
Honolulu Airport
27h 09m
Trip: 15 days
Based on null reviews
Tue, Sep 8
OGG
Kahului Airport
ORD
Chicago O'Hare Airport
11h 39m
Tue, Sep 15
ORD
Chicago O'Hare Airport
OGG
Kahului Airport
14h 38m
Trip: 8 days
Based on null reviews
Mon, Aug 24
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
20h 32m
Sun, Sep 6
ORD
Chicago O'Hare Airport
HNL
Honolulu Airport
27h 29m
Trip: 14 days
Based on null reviews
Wed, Aug 19
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
20h 32m
Mon, Aug 24
ORD
Chicago O'Hare Airport
HNL
Honolulu Airport
25h 59m
Trip: 6 days
Based on null reviews
Tue, Aug 11
OGG
Kahului Airport
ORD
Chicago O'Hare Airport
23h 22m
Tue, Sep 8
ORD
Chicago O'Hare Airport
OGG
Kahului Airport
24h 59m
Trip: 29 days
Based on null reviews
Wed, Sep 16
OGG
Kahului Airport
ORD
Chicago O'Hare Airport
11h 39m
Sun, Sep 20
ORD
Chicago O'Hare Airport
OGG
Kahului Airport
14h 38m
Trip: 5 days
Based on null reviews
Tue, Sep 1
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
23h 35m
Sun, Sep 13
ORD
Chicago O'Hare Airport
HNL
Honolulu Airport
34h 10m
Trip: 13 days
Based on null reviews
Wed, Aug 12
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
20h 27m
Thu, Aug 20
ORD
Chicago O'Hare Airport
HNL
Honolulu Airport
29h 38m
Trip: 9 days
Based on null reviews
Thu, Sep 17
LIH
Lihue
ORD
Chicago O'Hare Airport
13h 49m
Mon, Sep 21
ORD
Chicago O'Hare Airport
LIH
Lihue
16h 37m
Trip: 5 days
Based on null reviews
Wed, Aug 12
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
20h 27m
Thu, Aug 20
ORD
Chicago O'Hare Airport
HNL
Honolulu Airport
27h 29m
Trip: 9 days
Based on null reviews
Sun, Aug 16
OGG
Kahului Airport
ORD
Chicago O'Hare Airport
17h 46m
Tue, Sep 8
ORD
Chicago O'Hare Airport
OGG
Kahului Airport
14h 33m
Trip: 24 days
Based on null reviews
Wed, Aug 12
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
20h 32m
Thu, Aug 20
ORD
Chicago O'Hare Airport
HNL
Honolulu Airport
25h 59m
Trip: 9 days
Based on null reviews
Sat, Dec 12
KOA
Kona Intl
ORD
Chicago O'Hare Airport
11h 23m
Tue, Dec 15
ORD
Chicago O'Hare Airport
KOA
Kona Intl
17h 33m
Trip: 4 days
Based on null reviews
Wed, Aug 12
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
20h 27m
Thu, Aug 20
ORD
Chicago O'Hare Airport
HNL
Honolulu Airport
25h 59m
Trip: 9 days
Based on null reviews
Wed, Sep 16
OGG
Kahului Airport
ORD
Chicago O'Hare Airport
33h 41m
Wed, Sep 23
ORD
Chicago O'Hare Airport
OGG
Kahului Airport
28h 52m
Trip: 8 days
Based on null reviews
Thu, Sep 17
OGG
Kahului Airport
ORD
Chicago O'Hare Airport
11h 39m
Mon, Sep 21
ORD
Chicago O'Hare Airport
OGG
Kahului Airport
14h 38m
Trip: 5 days
Based on null reviews
Tue, Sep 15
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
14h 56m
Sat, Sep 19
ORD
Chicago O'Hare Airport
HNL
Honolulu Airport
32h 30m
Trip: 5 days
Based on null reviews
Sun, Aug 16
KOA
Kona Intl
ORD
Chicago O'Hare Airport
16h 33m
Sun, Aug 23
ORD
Chicago O'Hare Airport
KOA
Kona Intl
14h 46m
Trip: 8 days
Based on null reviews
Tue, Sep 8
OGG
Kahului Airport
ORD
Chicago O'Hare Airport
23h 10m
Tue, Sep 15
ORD
Chicago O'Hare Airport
OGG
Kahului Airport
32h 00m
Trip: 8 days
Based on null reviews
Thu, Aug 13
KOA
Kona Intl
ORD
Chicago O'Hare Airport
21h 17m
Mon, Aug 17
ORD
Chicago O'Hare Airport
KOA
Kona Intl
14h 56m
Trip: 5 days
Based on null reviews

Book cheap flights from Hawaii to Chicago (one-way)

Airports
Origin
Kahului
$428
only
$428
Hilo
$411
only
$411
Honolulu
$155
only
$155
Lihue
$174
only
$174
Kailua-Kona
$202
only
$202
Destination
Chicago
$155
only
$155
$247
only
$247
Tue, Oct 13
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
27h 34m
Based on null reviews
Mon, Oct 12
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
21h 35m
Based on null reviews
Tue, Sep 8
KOA
Kona Intl
ORD
Chicago O'Hare Airport
14h 04m
Based on null reviews
Sat, Aug 22
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
21h 31m
Based on null reviews
Wed, Aug 19
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
23h 20m
Based on null reviews
Wed, Oct 7
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
13h 26m
Based on null reviews
Sat, Sep 12
ITO
Hilo Intl
ORD
Chicago O'Hare Airport
20h 50m
Based on null reviews
Wed, Sep 9
LIH
Lihue
ORD
Chicago O'Hare Airport
37h 48m
Based on null reviews
Mon, Aug 10
OGG
Kahului Airport
ORD
Chicago O'Hare Airport
22h 50m
Based on null reviews
Sat, Aug 8
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
45h 21m
Based on null reviews
Thu, Aug 20
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
19h 37m
Based on null reviews
Mon, Oct 12
HNL
Honolulu Airport
MDW
Chicago Midway Airport
15h 38m
Based on null reviews
Mon, Oct 12
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
35h 41m
Based on null reviews
Sat, Aug 22
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
20h 51m
Based on null reviews
Wed, Oct 7
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
15h 49m
Based on null reviews
Thu, Aug 13
OGG
Kahului Airport
ORD
Chicago O'Hare Airport
20h 44m
Based on null reviews
Mon, Aug 10
OGG
Kahului Airport
ORD
Chicago O'Hare Airport
18h 53m
Based on null reviews
Wed, Aug 12
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
20h 32m
Based on null reviews
Sat, Aug 22
HNL
Honolulu Airport
ORD
Chicago O'Hare Airport
21h 31m
Based on null reviews
Tue, Sep 8
LIH
Lihue
ORD
Chicago O'Hare Airport
13h 49m
Based on null reviews
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

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